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Cholic acid (M2MDB001819)

Record Information
Version2.0
Creation Date2012-08-09 09:16:12 -0600
Update Date2015-09-16 14:50:11 -0600
Secondary Accession Numbers
  • ECMDB21424
Identification
Name:Cholic acid
DescriptionCholic acid is involved in absorption of fat and cholesterol excretion.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triol
  • 3a,7a,12a-Trihydroxy-5b-cholan-24-oate
  • 3a,7a,12a-Trihydroxy-5b-cholan-24-oic acid
  • 3a,7a,12a-Trihydroxy-5b-cholanate
  • 3a,7a,12a-Trihydroxy-5b-cholanic acid
  • 3a,7a,12a-Trihydroxy-5b-cholanoate
  • 3a,7a,12a-Trihydroxy-5b-cholanoic acid
  • 3a,7a,12a-Trihydroxy-b-cholanate
  • 3a,7a,12a-Trihydroxy-b-cholanic acid
  • 3a,7a,12a-Trihydroxy-beta-cholanate
  • 3a,7a,12a-Trihydroxy-beta-cholanic acid
  • 3a,7a,12a-Trihydroxy-β-cholanate
  • 3a,7a,12a-Trihydroxy-β-cholanic acid
  • 3a,7a,12a-Trihydroxycholanate
  • 3a,7a,12a-Trihydroxycholanic acid
  • 5b-Cholanate-3a,7a,12a-triol
  • 5b-Cholanic acid-3a,7a,12a-triol
  • 5b-Cholate
  • 5b-Cholic acid
  • Cholalate
  • Cholalic acid
  • Cholalin
  • Cholate
  • Colalin
Chemical Formula:C24H40O5
Weight:Average: 408.5714
Monoisotopic: 408.28757439
InChI Key:BHQCQFFYRZLCQQ-IATNSQEUSA-N
InChI:InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19?,20+,22+,23+,24-/m1/s1
CAS number:81-25-4
IUPAC Name:(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name:(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
SMILES:[H][C@@](C)(CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@]([H])(O)[C@]12C
Chemical Taxonomy
Description belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 12-hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-1
Melting point:197-201 °C
Experimental Properties:
PropertyValueSource
Water Solubility:0.175 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:2.02 [RODA,A ET AL. (1990)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.074 g/LALOGPS
logP2.26ALOGPS
logP2.48ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.79 m³·mol⁻¹ChemAxon
Polarizability46.95 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Cholic acid + NAD <> NADH + Hydrogen ion
Cholic acid + NAD <> NADH + Hydrogen ion
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0000900000-808c992335220d55eb9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-0000900000-4d45fc21c585f246a9b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0ap4-9184300000-4f617757041cb4124546View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0009000000-f5b70cbc59d5ea066854View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0009000000-b06963261afb6fdb494bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02c2-2109000000-576432f702c3825dd919View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0009700000-8dc05bd9542a54f1f91bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0009200000-9a24af3f58b590ac86cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9007000000-c0f6af27285559bd789eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16359
HMDB IDHMDB00619
Pubchem Compound ID221493
Kegg IDC00695
ChemSpider ID17216023
WikipediaCholic acid
BioCyc IDNot Available

Enzymes

Protein Details
1. 7-alpha-hydroxysteroid dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
7-alpha-dehydroxylation of cholic acid, yielding deoxycholic acid and lithocholic acid, respectively. Highest affinity with taurochenodeoxycholic acid
Gene Name:
hdhA
Uniprot ID:
P0AET8
Molecular weight:
26778
Reactions
3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate + NAD(+) = 3-alpha,12-alpha-dihydroxy-7-oxo-5-beta-cholanate + NADH.